The upside of life as an IT contractor is alluring. You get to be your own boss, accept only the jobs you want, and work flexible hours. With each assignment comes the opportunity to learn new skills and gain exposure to different environments.

But there are obvious sacrifices – job security and paid vacations, for starters. As an IT contractor, you’re also often responsible for your own benefits (healthcare, retirement), paying taxes, and marketing yourself for the next gig.

Tech pros who successfully balance the pros and cons of contracting play an important role in the IT world. They provide manpower when workloads spike and can bring key expertise or niche skills to a team. In recent years, companies have increasingly relied on a contingent workforce to augment their full-time staff. In a new survey by TEKsystems, more IT leaders said they expect to increase temporary hiring (42%) than those who plan to increase full-time hiring (37%).

On the jobs front, contingent workers make up a significant percentage of open positions. In early October, there were 36,262 contract positions posted on IT careers site Dice.com, representing 44% of the 81,554 total available tech jobs.

“I like the freedom and flexibility to set my own schedule,” says Ken Rubin of High Road Data, which provides IT consulting, web design, and programming services in Orange County, Calif. “When I worked for enterprises, I couldn't do any banking or go to the post office. Everything I needed to do personally seemed to fall in the business hours I was at work. Plus, I've been able to walk my kids to school and spend time with them in the mornings. That’s priceless.”

Jerry McKune, an independent IT contractor based in the St. Louis area, appreciates the variability of IT contracting and the opportunity to keep learning new skills. “I love variety. I cannot stand to do the same thing over and over and over again. There’s a lot of variety in the contract world.”

The challenge of variety, however, is that each new assignment means a new learning curve. “Education takes time,” McKune says. “If you’re on a six-month contract, and there’s a four- to five-month learning curve, there’s only going to be a short period of time at the end of it where you really know what you’re doing and you’re capable of performing the tasks assigned to you without help from somebody else.”

Learning to rely on other people and not being afraid to say you don’t know something are essential traits. “There are going to be a lot of situations as a contractor where you don’t know the answer. Do not tap dance. Just simply say, ‘I don’t know. But I’ll find out and I’ll get back to you within 24 hours,’” McKune says. “That’s a very powerful response.”

Employers and contract workers value flexibility

The appeal of contingent workers has risen since the recession; companies today are looking to build lean, agile IT departments that can adapt to changing business requirements, says Jason Hayman, market research manager at IT staffing and services firm TEKsystems. With temporary workers, companies can bring on skilled IT talent to handle specific projects and scale back if demand falls.

“We’re seeing a more blended workforce today, of a smaller W-2 [full-time] workforce and a growing variable workforce,” says Peter Cannone, CEO of OnForce, which run a cloud-based marketplace for hiring independent IT workers. The platform connects companies that need IT help for short-term assignments with IT freelancers who've been vetted by OnForce (in a typical month, just 10% of the 1,000 who apply to join the community are accepted).

Part of the appeal for contractors is the opportunity to build their own businesses, Cannone says. “Once you get a taste of being your own boss, and running your own business, I think it’s hard to go the other way.”

Contractors agree -- being the boss is appealing.

“I still make mistakes, but they are my mistakes. I own them and it is my responsibility to fix them. I am my own (pointy-haired) boss,” says Fred Granville, who has been working as an independent networking consultant in the Kansas City, Mo., area since 2000.

“We’re always looking for people who have the ability to work on different projects, keep themselves on track, set their own times, be their own boss,” says Vik Nath, director of recruitment in the Washington, D.C., office of IT staffing services provider Mondo. “If you’re hiring a contractor, and you’re hiring them for a specific project, you’d like to just let them run with it. You need to find that skill set, find that person who doesn't need to be micromanaged.”

Access to new or different technology is another perk that resonates with contractors.

“I like being able to get hands-on with equipment that I would never get anywhere near otherwise,” says Jodi Minshall, an IT analyst in the San Francisco Bay area. Minshall recently completed an assignment at Juniper Networks and got to work with the vendor’s extremely large core routers for the ISP market. “At any other company these devices would be in a locked room with a select few employees tasked with managing them, and I might be able to see them through a window if I were lucky.”

Getting busy – and staying busy

IT contractors are frank about the challenges of contingent work. In particular, lining up the next job is an inescapable part of the lifestyle.

“The hardest part about being a contractor is finding work. When you work for yourself, you must fill the roles of executive, business administration, AR/AP, sales, engineering, delivery, and probably a few others,” says Mike Drabicky, who has worked as a consultant for 15 of the last 20 years. “I like doing the work. All the rest of that stuff is overhead that, while necessary, doesn't produce anything useful.”

Marketing can be a challenge. “As with most technical folks, it doesn't come naturally,” says Rubin of High Road Data. “I am a member of [business networking group] BNI and make extra effort every week to get together with other business owners and professionals to meet and learn how we can help refer each other. Since I’m not trained in marketing, I find this an invaluable tool to get myself out there and make sure I’m constantly marketing.”

Getting paid is another potential hurdle. “If you’re not working with a company that farms you out and does the billing and collections for you, then you have to do this yourself,” Rubin says. “You need to manage a positive relationship with your clients and at the same time make sure they pay on time, every time.”

Jodie Bass finds much of his work through the OnForce freelance platform. OnForce work orders are backed by reserved funds, so payment is transferred directly to the contractor once work is completed. For Bass, the elimination of invoicing and payment collection is a huge draw.

“I hate talking about money,” says Bass, who’s based in the Portland, Ore., area. “I’m not a salesman. I can get people excited about technology. I can teach them how to use it and support it later. But when it comes time for me to say, ‘ok, write me a check,’ I’m terrible about it.” OnForce takes a percentage of the job funds as payment, but that’s ok with Bass. “I look at it this way: I don’t pay for advertising, I don’t pay for collections. Both of those are covered. The fee is worth it.”

Loss of job security is a lingering concern

Minshall misses the benefits that full-time employees enjoy, such as sick time, holiday pay, training and retirement benefits. But the biggest loss is job security.

“The hardest part is not having the security of a real two-way bond with your employer/customer,” Minshall says. “As a contractor you can be replaced at the drop of a hat with no explanation or recourse. ‘Here today and gone tomorrow’ has a whole new meaning for a contractor.”

Sometimes, that insecurity can be viewed as an advantage: “It keeps me honest as an employee,” says Nancy Silverthorn, an IT contractor based in Charlotte, N.C. “You stay at the top of your game knowing that at any time they could sever that connection. It’s a lot easier to sever a contract connection” than a full-time connection.

Minshall stresses the importance of self-discipline. “You have to be very proactive about securing your own future with savings and self-educating to get ready for your next employment search. Living paycheck to paycheck is not an option for a contractor; you have to be financially prepared for the worst.”

Otherwise, life can be pretty grim in between assignments.

“Starve to death, scrounge up spare money selling bottles and cans from the garbage, [beg] former co-workers for insight and opportunities,” says Joe Holcomb of his activities when he’s in between contracts.

The stress of being unemployed in between assignments is the hardest part for Holcomb, who also cites the “inconsistency of income” and “low-ballers that want to hire you for less than they would pay an employee,” among his dislikes. “New work, unique business environments” are the pluses of contracting life for Holcomb.

Independent contractors also have to get used to not having paid vacations.

“In the last seven years (other than days like Thanksgiving and Christmas), I have taken four days off,” Drabicky says. “When you do consulting, you don’t have weekdays or weekends; rather, you have days that you work, and days that you don’t work. If you want a day off, you can certainly do so but they are without pay. It would be nice to have some time to decompress and still have some pay coming in.”

Drabicky also misses being part of a team. “I find it loads of fun to be part of a quality team, of people who want to excel, want to make a difference. The best times I've had working are when we had a good team where folks were willing to do whatever it took to benefit the team,” Drabicky says. “You can sometimes get that as a consultant. Most times, everyone knows you’re only on board for a limited time. This makes forming lasting relationships difficult to impossible.”

Still, there are valuable relationships that can come from contracting assignments.

“The opportunity to meet people, to make additional contacts, and have your name passed on to somebody else is a huge benefit. In my view, maybe the best of all the benefits,” McKune says.

It’s not something he takes for granted, however: “Networking is a lot more work than people believe it is,” McKune says. “From my perspective, it requires quite a bit of work to maintain those relationships and keep those networking contacts going.”

For Minshall, any gap between assignments is an opportunity to sharpen IT skills.

“I like to spend a few days offloading accumulated stress and catching up on household chores. After a few days of that, I start researching new IT trends and trying to polish up my rusty skills,” Minshall says of his downtime between contracts. “Every job emphasizes one set of skills more than others, so you tend to get out of practice with the unused portion of your skills set. I like to brush up on my skills to stay current.”

Longtime independent consultant Granville finds some challenges for contractors are no different from those faced by full-time IT employees.

“Early on, the peaks and valleys of activity were disconcerting. Now I just get frustrated during those times when I am unable to respond quickly to my customers,” Granville says. “Occasionally the hours can be long, but I think that is true for any job. Balancing family life and work life is probably difficult for all IT workers.”

On the plus side, Granville cites a number of other things he likes about the IT contract life: being able to do what he thinks is the right thing for his customers; working with customers he likes; the chance to define his own target market; and a flexible schedule. His ideal assignments are those that allow him to architect and build new network designs.

Temp-to-perm temptations

Independent contracting isn't a lifestyle for everyone. “There’s obviously risk involved in going that route – as the name suggests, it’s temporary, not permanent,” Hayman says.